Cyclopentylamine → HCID 10272182, compound

HRID 1830714Notes

Reaction equation

HRID 1830714 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)=[O:15])=[C:9]([O:23][CH3:24])[CH:8]=1)=[O:5].[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:25]1([NH:30][CH2:2][CH2:3][C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)=[O:15])=[C:9]([O:23][CH3:24])[CH:8]=2)=[O:5])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 22046434HCID 22046434, compound2×

Product 1

HCID 10272182HCID 10272182, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chloro-N-[3-methoxy-4-(3-pyrazin-2-yl-ureido)phenyl]-propionamide (Compound 8, Example 12) and cyclopentylamine (0.5 mL, large excess) was warmed at 80° C. for 1 h and cooled to room temperature. The product was precipitated from ether (10 mL), collected by filtration, washed with ether, and dried in vacuo (24 mg, 60%). 1H NMR (300 Mhz, d6-DMSO) δ: 10.14 (s, 1H), 10.03 (s, 1H), 9.93 (s, 1H), 8.87 (d, J=1.1 Hz, 1H), 8.31 (dd, J=2.6, 1.5 Hz. 1H), 8.23 (d, J=2.7 Hz, 1H), 8.03(d, J=8.7 Hz, 1H), 7.47,(d, J=2.1 Hz, 1H), 7.04(dd, J=8.7, 2.1 Hz, 1H), 3.87 (s, 3H), 3.05 (quintet, J=6.3 Hz, 1H), 2.80 (t, J=6.6 Hz, 2H), 2.44 (t, J=6.6 Hz, 2H), 1.80-1.67 (m, 2H), 1.65-1.56 (m, 2H), 1.53-142 (m, 2H), 1.37-1.27 (m, 2H). LRMS (ESI, positive) m/e 399.1 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. customThe product was precipitated from ether (10 mL)
  3. filtrationcollected by filtration
  4. washwashed with ether
  5. customdried in vacuo (24 mg, 60%)

Sources & evidence

ORD record
ord-430482049355459fa40a43a1f1c611df
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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